(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮 → L-脯氨酸甲酯盐酸盐

HRID 129573

反应方程式

HRID 129573 反应方程式
S(Cl)([Cl:3])=O.[NH:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=[O:8].[CH3:13]O>>[ClH:3].[NH:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([O:9][CH3:13])=[O:8]

参与物

4

反应物 3

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮HCID 24386氯化亚砜HCID 145742L-脯氨酸

产物 1

HCID 2733200L-脯氨酸甲酯盐酸盐收率 99.6%

实验过程

Thionyl chloride (65 ml, 0.89 mol) was added dropwise at ice-cooling for 45 min to a solution of L-proline (57.6 g, 0.50 mol) in 500 ml MeOH. The temperature was raised to reflux. After 4 h at reflux the mixture was cooled and the solvent evaporated in vacuo. MeOH was added to the residue and then evaporated repeatedly three times to give 86 g crude methyl (S)-2-pyrrolidinecarboxylate hydrochloride (99.6% purity by GLC) as a thick syrup. The ester (1.65 g, 0.01 mol) was transferred to a flask containing acetaldehyde (2.21 g, 0.05 mol) 10% Pd/C (0.15 g) and 15 ml MeOH. The mixture was shaken in a Parr apparatus at 55 psi hydrogen pressure for 4 h at room temperature, filtered and evaporated to give 2.1 g crude hydrochloride of the title ester. (91% purity by GLC). This material was subjected to aminolysis in Example 7D.

后处理

  1. temperatureThe temperature was raised
  2. temperatureto reflux
  3. temperatureAfter 4 h at reflux the mixture
  4. temperaturewas cooled
  5. customthe solvent evaporated in vacuo
  6. additionMeOH was added to the residue
  7. customevaporated repeatedly three times

来源与证据

ORD记录
ord-a970eee38a57465085b49457150c9b32
来源数据集
uspto-grants-1995_11
专利号
US05468876

关联笔记

加载中…